1. Carboxylic acid and carboxylic acid derivatives Carboxylic acid and carboxylic acid derivatives Dr. Nabila Al Jaber

2. Carboxylic acid R-COOH Ar-COOH Aliphatic (carboxylic cid) aromatic (benzoic acid) 1) replace ane by -ic acid Nomenclature : CommonIUPACFormula No. C Formic acid Acetic acid Prpionic acid Butyric acid valeric acid Salicylic acid Benzoic acid Methanoic acid Ethanoic acid Prpanoic acid Butanoic acid Pentanoic acid 2-hydroxy ben. a HCOOH CH 3 COOH CH 3 CH 2 COOH CH 3 (CH 2 ) 2 COOH CH 3 (CH 2 ) 3 COOH 12345

3. 2) Longest continuous chain CH 3 CH 2 CHCH 2 CH 2 COOH 4-Methyl hexanoic acid CH 3      C-C-C-C-C-COOH CH 3 CH 2 CHCH 2 CH 2 COOH γ-Methyl hexenoic acid CH 3

4. commmone:  -  - Dimethyl butyric acid IUPAC: 2,3-Dimethyl butanoic a CH 3 -CHBr-CHCl-CO 2 H 3-Bromo-2-chlorobutnoic acid

5. 3) In cyclic ring ------ cycloalkane carb. a'

6. 5) Aromatic acid by common name

8. Physical properties 1] They form hydrogen 2] comp. 1-7 soli in H 2 O. 3] mor than 7 carbon less soli. (bec. R increased) 4] Aromatic acids insoluble. In H 2 O 5] BP. Acid > Alcohol

9. Deac. gps inc. acidity Acti gps dec. acidity

10. HCOOH > CH 3 COOH > CH 3 CH 2 COOH > CH 3 CH 2 CH 2 COOH More acidity Substitution with halogen : CH 3 CH 2 COOH < CH 2 Cl-CH 2 COOH (more acidic) CH 3 CH 2 COOH < CH 2 ClCOOH < CHCl 2 COOH < CCl 3 COOH More acidity

11. Preparation of carboxylic acid 1] Oxidation a) 1  alcohols & Aldehydes

12. Preparation of carboxylic acid

13. b) of alkyl benzene

14. 2)Hydrolysis of nitriles

15. 3] Carbonation of Grignard reagent:

16. Preparation of carboxylic acid Hofmann Reaction Hofmann Reaction Collb’s Reaction Collb’s Reaction

17. Reactions of acids 1)Salt formation: it react with strong base & we can use CaOH, NaOH or KOH

18. reaction with weak base Sodium bicarb. Can be used to distinguish between carboxylic acid and phenols Reactions of acids

19. 2) Formation of Easter: 3) Formation of amide: Reactions of acids

20. 4) Formation of acid anhydride: 5) Formation of acid chloride: Reactions of acids

21. Addition anti marco.

22. Nomenclature of carboxylic acid derivatives When Oxygen of Carboxylic acid is replaced with Nu.------ Carb. a' deriv

24. 1] Salt:

25. 2] Acid chloride

26. 3] Ester: The alkyl gp. Named 1st then the name of parent acid with ending – ate in place of -ic acid

28. 4]Amides: -oic acid or -ice a' by – amide.f 1 or 2 subst. on nitrogen we say N-subs. or N,N-disubs. (sub. Name 1st )

30. 4] Acid anhydride: replacing -acid with anhydride

31. R-CO-Cl > R-(CO) 2 O-R > RCO 2 R > RCO 2 H > RCONH 2 Acid chloride Acid anhydride Ester Acid Amide Order of reaction: Benzoic acid anhydride

32. AMIDESAMIDES

33. ESTER S

34. ANHYDRIDESANHYDRIDES

35. Overview Reaction

36. Reactions of acid derivatives a) Acid chlorides: Reduction:

37. B] Acid anhydride: Reduction:

38. C] Esters: Reduction:

39. d] Amide: Reduction: Dehydration: Hoffman degradation: